Benzo-1,3-dioxole-5-methylamine → HCID 131721756, compound

HRID 1004145Notes

Reaction equation

HRID 1004145 reaction equation
[CH2:1]([NH2:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[CH2:12]([CH2:27]/[C:28](/[CH3:37])=[CH:29]/[CH2:30][CH2:31]/[C:32](/[CH3:36])=[CH:33]/[CH2:34]Br)[CH:13]=[C:14]([CH2:16][CH2:17][CH:18]=[C:19]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH3:20])[CH3:15]>C1COCC1>[CH2:12]([CH2:27]/[C:28](/[CH3:37])=[CH:29]/[CH2:30][CH2:31]/[C:32](/[CH3:36])=[CH:33]/[CH2:34][NH:11][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)[CH:13]=[C:14]([CH2:16][CH2:17][CH:18]=[C:19]([CH2:21][CH2:22][CH:23]=[C:24]([CH3:26])[CH3:25])[CH3:20])[CH3:15]

Participants

4

Reactant 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 131721757HCID 131721757, compound

Product 1

HCID 131721756HCID 131721756, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 40 ml of THF was dissolved 7.56 g of piperonylamine, a solution of 2.11 g of farnesylgeranyl bromide in 10 ml of THF was added dropwise at room temperature and stirred at room temperature for 12 hours. Then, the THF was concentrated under reduced pressure. The concentrate was dissolved in chloroform and then washed with a 5% sodium hydroxide solution. After the chloroform layer was concentrated under reduced pressure, the concentrate was dissolved in acetonitrile and extracted with hexane (150 ml×2). The hexane layer was washed with acetonitrile (50 ml×2) and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (using ethyl acetate as a developing solvent) to give 2.0 g of N-farnesylgeranylpiperonylamine as a yellow oily substance.

Workup

  1. concentrationThen, the THF was concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in chloroform
  3. washwashed with a 5% sodium hydroxide solution
  4. concentrationAfter the chloroform layer was concentrated under reduced pressure
  5. dissolutionthe concentrate was dissolved in acetonitrile
  6. extractionextracted with hexane (150 ml×2)
  7. washThe hexane layer was washed with acetonitrile (50 ml×2)
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by silica gel column chromatography (

Sources & evidence

ORD record
ord-a18552f263e84b6aa42f02e0f50369da
Source dataset
uspto-grants-2000_04
Patent number
US06048882

Reaction notes

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